I-Team: Tracking Down The State’s Worst Tax Delinquents

BOSTON (CBS) – Most taxpayers just assume they have to file tax returns every year and pay what they owe, or else.

But the I-Team has found that’s not necessarily the case, even for people who owe the state millions of dollars.

Robert Green and Heather O’Loughlin, husband and wife, get around in a Lexus SUV and live in a Charlestown townhouse.

O’Loughlin is an investment analyst. Green is a lawyer. The state of Massachusetts says they haven’t been paying their taxes.

A whole lot of taxes.

We asked Green how their tax debt to the state got to be more than $8 million.

“Do you really think it’s honestly that?” he asked.

The Massachusetts Department of Revenue certainly thinks it is. It’s there for anyone to see on DOR’s website, which lists the state’s 10 biggest tax delinquents. The state says O’Loughlin owes $8.98 million.

But O’Loughlin and Green told the I-Team they actually don’t owe all that money in back taxes, insisting the state has made a huge error by assuming the couple made millions on stock deals.

“I know it looks from bookkeeping like a large amount of money, but if you buy something and sell it at a loss… it doesn’t mean you made that much money,” Green said.

O’Loughlin and Green aren’t even the top tax delinquents on DOR’s list.

Number one is Theodore Moy of Wellesley. The state’s tax collection agency says Moy owes more than $9.5 million.

The problem for DOR is that Mr. Moy no longer lives in the million-dollar home in Wellesley where they have him listed. In fact, he hasn’t lived here in eight years, and for now anyway, Moy is nowhere to be found.

“Look, it’s not the result we want,” said DOR Commissioner Amy Pitter, insisting the department has a good track record when it comes to chasing down delinquents.

“Obviously we prioritize high-dollar cases,” Pitter said. “You can get the most money where the most money is owed.”

But that may not work out in Moy’s case.

In a bankruptcy filing obtained by the I-Team, Moy listed more than $2.2 million in liabilities, including about $250,000 in credit card debt.

We asked the DOR commissioner if there’s a chance the state will never see any money from some of its biggest debtors.

“It depends on the situation,” she said. “If somebody is really dead broke, chances are we’ll never see the money.”

O’Loughlin and Green gave the Department of Revenue years of outstanding tax returns Wednesday, complying with a court order.

They now claim they don’t owe the state anything. In fact, they say the state will owe them a refund of almost $1,500.

Overall, 633 people currently owe the state more than $25,000 in unpaid taxes. That adds up to more than $134 million.